4-Toluenesulfonyl chloride → N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide

HRID 2192158ノート

反応式

HRID 2192158 の反応式
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=2[F:22])[NH:4][CH:3]=1.C([Li])CCC.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=2[F:22])[N:4]([S:34]([C:31]2[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[CH:3]=1

参加物

6

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 59741015N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}acetamideHCID 178418339Butyllithium

生成物 1

HCID 59740993N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

3.23 g (8.87 mmol) of N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}acetamide are dissolved in 500 ml of THF and cooled to −78° C. 3.90 ml (9.76 mmol) of a 2.5M n-butyllithium solution are added, and the mixture is stirred for 15 min. 1.86 g (9.76 mmol) of p-toluenesulfonyl chloride are then added dropwise as a solution in 20 ml of THF. The reaction solution is allowed to warm to RT and stirred for one hour. Sodium bicarbonate solution is then added, and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is removed under reduced pressure.

後処理

  1. temperatureto warm to RT
  2. stirringstirred for one hour
  3. extractionthe mixture is extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. customthe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-ac1b308175fd4fd09c730cf0f091a29f
出典データセット
uspto-grants-2012_12
特許番号
US08329716B2

反応ノート

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